What are some discreet restaurants/ bars that you'd recommend for dates and meet & greets with clients? Places that are upscale but lowkey on weekday evenings.
 
And please don't say Tavern/Gibson's...

Outback, Texas Longhorn, Olive Garden. These restaurants are low key. But upscale enough not to be cheap.  

You're kidding right?

Nico Osteria and Boarding House are very discreet and well decorated. I've also had a decent experiences at River Roast and Joe's Seafood.

Lmao, I hope so :\

upscale... hahahaha

Bandara on Michigan Avenue is always crowded but a
It is all booths for 2 or larger ones. It's quite dark in the evening except for one spot on the table.  

I'd say it meets all your criteria

once a year specials

Considering that's where he works as a dishwasher lol

Check out yelp for date spots.

A table by the window has a magnificent view of the Water Tower and I find it to be secluded with rather subdued lighting.

Love Bandera and it is a great spot.  Here are some of my other favorites.  My brother and I always challenge ourselves to get the best answers to this question.  So funny that it was asked here.  

The Franklin Room on, of course, Franklin between Erie and Huron. A little on the spendy side, but the food and drinks are quite good.

dim and romantic!  Plus, you won't be able to tell if your date actually looks good or if it's just the drinks and lighting...

I second Boarding House!

I'd also add Chicago Cut Steakhouse and Black Bird. The staffs are both very good about discretion. Heads up, Black Bird is a little smaller and the seating arrangement is a little more exposed if visibility is something you'd like to avoid.